Once upon a time, city tours highlighted all that was picture perfect about Vancouver: parks and beaches, bustling streets and vibrant shopping, museums and more.

But it turns out that showing off the city’s bad side can be just as fun.

Over the last few years, a bevy of tours have cropped up that focus on exploring Vancouver’s dark and often tawdry past. For anyone interested in learning a bit about the city’s dirty laundry, these five tours are wicked good fun:

Lost Souls of Gastown: This tour from Forbidden Vancouver harkens back to the late 1800s, when Vancouver was still a violent frontier town. Guests walk Vancouver’s oldest streets while trained actors in historical dress evoke the chaos of the early city, plagued by cataclysmic fires, smallpox outbreaks, filthy brothels and thuggish gold prospectors. Learn more.

Vice, Dice and Opium Pipes: Accompanied by a guide, guests troll the mean streets of Gastown and Chinatown, exploring the one-time opium dens and brothels of Shanghai Alley, learning about daylight murders and uncovering the police corruption scandals of the 1920s. (This tour is the second coming of the Vancouver Police Museum‘s Sins of the City, which started the “bad” tour craze years ago.) Learn more.

Prohibition City Tour: On this tour, guests are pressed into service as undercover newspaper reporters in prohibition-era Vancouver. When the province officially went dry back in 1917, organized crime and corruption exploded. While peeking into some of the city’s iconic heritage buildings, visitors are called upon to track down Vancouver’s most infamous mayor, most exotic showgirl and most prolific rum-runner. Learn more.

Secrets of the Penthouse: Ready to venture inside of one of Vancouver’s oldest and most notorious gentlemen’s clubs? Forbidden Vancouver takes visitors backstage at the Penthouse to hear stories from the club’s longtime owner and even sit in on a live burlesque show. Since 1947, the club has seen more than its share of drama – from murders and robberies to fires, police raids and even a few visits from Frank Sinatra. Learn more.

Gastown Craft Beer ‘n Bites Tour: OK, this last tour isn’t quite as dark and sinister as the rest, but it’s still pretty decadent. In the company of a “passionate beer educator” from Vancouver Food Tours, guests pop into three of Gastown’s finest pubs for samplings of craft beers from Vancouver and beyond. Drinks are paired with modern gastropub snacks and ample attention is given to the lurid secrets of craft brewing. Learn more.

Did I miss any other sinful tours of Vancouver? Let me know below.

For more updates on Vancouver and beyond, follow me on Twitter @RemyScalza.

Inside Vancouver is a multi-author blog, written by Vancouverites about Vancouver. Our goal is to give an insider’s view of Vancouver, to provide information, stories and opinions from the locals’ perspective about this great city.